Dave Chappelle’s 10 Best Movie Roles

As he proved with his stand-up and the brilliant sketch series Chappelle’s Show, Dave Chappelle is one of the funniest people on the planet. But he’s also popped up in a few movies, energizing the smallest cameo or carrying a whole comedy. With The Nutty Professor airing this month on IFC, we’re paying tribute to Dave Chappelle’s best big screen roles.

10. Rusty P. Hayes, Screwed

Universal

In this dark Norm MacDonald comedy, Dave’s Rusty P. Hayes helps a bedraggled chauffeur kidnap his rich employer’s yappy dog to earn a million dollar ransom. Naturally, things go hilariously wrong. Dave is never funnier than when faced with the idiocy of others, even when he enabled them every step of the way.

9. Kevin, You’ve Got Mail

Warner Bros.

Yep, there was a time (the ’90s) when Dave Chappelle was in a Tom Hanks/Meg Ryan movie. Not the place you’d picture him, but his character Kevin Jackson is on hand to help Tom and Meg get on with their lives and realize the obvious love between them.

8. Tulley, Blue Streak

Columbia Pictures

Chappelle crams comedy into Tulley, the movie’s most unfortunate character. Tulley can’t quite get away from a double-crossing criminal out for revenge, a diamond-thief-turned-fake-policeman, and quite a lot of very real policemen.

7. Disco Cabbie, 200 Cigarettes

MTV Films

Set on New Year’s Eve of 1981 (but released in 1999), 200 Cigarettes features a “who’s who” of Clinton-era stars — everyone from Christina Ricci to Courtney Love — trying to make it in the big city. But Dave Chappelle’s Disco Cabbie isn’t struggling with anything. Disco Cabbie knows exactly who he is and where he’s going. With a character name like Disco Cabbie you don’t even need the rest of the script — just point the camera on Dave and let him go.

6. Pinball Parker, Con Air

Touchstone Pictures

Pinball Parker proves that his powers extend to getting everyone’s attention and bringing the house down even when that house is a heavily guarded plane full of convicted felons. Dave improvised most of his lines in this Nic Cage action flick, and they’re some of the best ones in the movie.

5. Reggie Warrington, The Nutty Professor

Universal

The first revenge taken by the jelly-Jekyll-to-high-fitness-Hyde transformation of Sherman Klump in The Nutty Professor is against Reggie Warrington, a brutal insult comic. And giving Chappelle cart blanche to be as evil as possible is comedy gold. Even his name is an insult, chosen to mock the director of an earlier movie Eddie Murphy had appeared in.

4. Ahchoo, Robin Hood: Men in Tights

Brooksfilms

Chappelle’s first film appearance as Ahchoo in the Mel Brooks comedy Robin Hood: Men in Tights demonstrated his ability to steal a scene from the movie’s stars, and hinted to his future greatness to come.

3. Morris, Chi-raq

40 Acres and a Mule Productions

Dave’s most recent film role was in Spike Lee’s satire about gang violence in Chicago. When the women of Chicago withhold sex from men involved in gang violence, Dave’s strip club owner character is devastated by the loss.

2. Conspiracy Brother, Undercover Brother

Universal Pictures

Undercover Brother is an underrated spoof of blaxploitation films, and Dave’s “Conspiracy Brother” adds to the hilarity on display. People turn to him and ask “Conspiracy Brother, what do you think?,” and the result is always amazing.

1. Thurgood Jenkins/Sir Smoke-a-Lot, Half Baked

Universal Pictures

While Thurgood Jenkins gets plenty of good lines, it’s Dave’s rapper character Sir Smoke-a-Lot that really allows him to let his comedy freak flag fly. We suspect Sir Smoke-a-Lot and Rick James are related.

The Best Of The Last

The end is near. In mere days Portlandia wraps up its final season, and oh what a season it’s been. Lucky for you, you can watch the entire season right now right here and on the IFC app, including this free episode courtesy of Subaru.

But now, let’s take a moment to look back at some of the new classics Fred and Carrie have so thoughtfully bestowed upon us. (We’ll be looking back through tear-blurred eyes, but you do you.)

Couples Dinner

It’s not that being single sucks, it’s that you suck if you’re single.

Cancel it!

A sketch for anyone who has cancelled more appointments than they’ve kept. Which is everyone.

Forgotten America

This one’s a “Serial” killer…everything both right and wrong about true crime podcasts.

Wedding Planners

The only bad wedding is a boring wedding.

Disaster Hut

It’s only the end of the world if your doomsday kit doesn’t include rosé.

Your Portlandia Personality Test

Carrie and Fred understand that although we have so much in common, we’re each so beautifully unique and different. To help us navigate those differences, Portlandia has found an easy and honest way to embrace our special selves in the form of a progressive new traffic system: a specific lane for every kind of driver. It’s all in honor of the show’s 8th and final season, and it’s all presented by Subaru.

Ready to find out who you really are? Match your personality to a lane and hop on the expressway to self-understanding.

Lane 10: Trucks Piled With Junk

Your junk is falling out of your trunk. Shake a tail light, people — this lane is for you.

Lane 33: Twins

You’re like a Gemini, but waaaay more pedestrian. Maybe you and a friend just wear the same outfits a lot. Who cares, it’s just twinning enough to make you feel special.

Lane 27: Broken Windows

Bad luck follows you around and everyone knows it. Your proverbial seat is always damp from proverbial rain. Is this the universe telling you to swallow your pride? Yes.

Lane 69: Filthy Cars

You’re all about convenience. Getting your car washed while you drive is a no-brainer.

Lane 43: Newly Divorced Singles

It’s been a while since you’ve driven alone, and you don’t know the rules of the road anymore. What’s too fast? What’s too slow? Are you sending the right signals? Don’t worry, the breakdown lane is nearby if you need it.

Still can’t find a lane to match your personality? Check out all the videos here. And see the final season of Portlandia this spring on IFC.

Last-Minute Holiday Gift Guide

It’s the final countdown to Christmas and thanks to IFC’s movie marathon all Christmas Eve and Christmas Day, you can revel in classic ’80s films AND find inspiration for your last-minute gifts. Here are our recommendations, if you need a head start:

Musical Instrument

Great analog entertainment substitute when you refuse to give your kid the Nintendo Switch they’ve been drooling over.

Breakfast In Bed

Any significant other or child would appreciate these Uncle Buck-approved flapjacks. Just make sure you’re not stuck on clean up duty.

Cocktail Supplies

You’ll need them to get through the holidays.

Dance Lessons

So you can learn to shake-shake-shake (unless you know ghosts willing to lend a hand).

Comfy Clothes

With all the holiday meals, there may be some…embigenning.

Get even more great inspiration all Christmas Eve and Day on IFC, and remember…